The New Water-soluble Phthalocyanine Synthesis And Properties

Due to the clear structure and compose, easy control of quality, and derivatives possessing well photosensitive property through modifying with different substituent groups, phthalocyanine (Pc) and its derivatives are considered to be a promising new photosensitive agents in photodynamic therapy (PDT). In this paper, the ArO group, which has been substituted by sulfonic group, was induced into the structure of phthalocyanine through the DBU method, and wishes to solve the questions of the phthalocyanine's transfer in body. Main research results are as follows:1. Based on synthesizing of nitrophthalonitrile through the nucleophilic reaction between 4- nitrophthalonitrile and potassium 1-sulfo-4-hydroxyl-benzene salt, four aqueous phthalocyanines derivatives no reported in the literature:PhSPcZn, PhSPcNi, PhSPcCo and PhSPcH₂, were papered by the DBU method, and were characterized by NMR, IR spectra, UV spectra, and element analysis.2. The studies of the solvable ability indicated that the water solvability of four phthalocyanine derivatives have been improved by introduction of 1-sulfophenoxy group. In addition, metal ions can affect the solvable property in different degree, and the soluble ability of PhSPcZn is highest than PhSPcNi, PhSPcCo and PhSPcH₂.3. Comparing with none substituted phthalocyanine, 1-sulfophenoxy group introduced can make theλ_max of metal phthalocyanines red shift for certain degree. Theλ_max will red shift acompany with the increase of d electron of the center metal ions and polar of solvents.4. The position of emission peak of PhSPcZn, PhSPcNi, and PhSPcCo was found red shift about 20nm compared with none substituted phthalocyanine. Phthalocyanines with center metal ions of anti-magnetism have the weaker fluorescence intensity, but with center metal ions of paramagnetic, their fluorescence intensity is stronger. With the increase of aggregated phthalocyanines, the fluorescence intensity decreases for self-quenching.5. Four phthalocyanine derivatives can produce the active oxygen radicals through the mechanisms of Typeâ… and Typeâ…¡. Phthalocyanines with center metal ions of the closed shell electron structure (such as Zn²⁺) have stronger photosensitive ability, but with center metal ions of open shell electron structure (such as Co²⁺, Ni²⁺), their photosensitive ability is weaker.6. According to the experiments of UV-vis spectra, fluorescence spectra, and the resonance light scatter, it can be found that there is one interaction occurring between PhSPcZn and CT DNA, and the interactive model is intercalation. Further, the photodamage property of PhSPcZn in oxygen condition has stronger photosensitive damage ability to the CT DNA.